Kevin O’Connor understands what a home can mean to a child because he remembers what it felt like to be embarrassed by his own.
“I grew up in Hyde Park. We were in rental housing, and I was always embarrassed about where I lived,” says O’Connor, who has served as CEO of the affordable housing nonprofit RUPCO since 2002. Years later, working in housing development, he walked a 10-year-old into his new bedroom in a house the boy’s parents had just purchased. The moment connected O’Connor’s childhood to the work that would consume his adult life. “That goes off the charts for me,” he says. “It informs the work.”
RUPCO is celebrating its 45th anniversary this year, marking nearly half a century of creating and managing affordable housing, helping first-time buyers purchase homes, administering rental assistance, restoring historic buildings, and providing supportive services throughout the Hudson Valley. Founded in 1981 as the Rural Ulster Preservation Company, the organization began as a program of the Ulster County Community Action Agency. Today it employs 120 people, manages 850 apartments, houses approximately 960 residents, and administers nearly 2,000 Section 8 vouchers in Ulster and Greene counties.
O’Connor has led RUPCO for more than half of its existence. When he arrived in 2002, after 14 years at Hudson River Housing in Poughkeepsie, the organization had 15 employees. RUPCO was based in Kingston and looking to expand its housing development work, an area in which O’Connor had considerable experience. It offered him his first chance to lead an organization. “I was number two there,” he says of Hudson River Housing. “It was a good opportunity to become number one, and I’m really grateful for the move.”
The scale and geographic reach have changed dramatically. RUPCO now works in six Mid-Hudson counties and is affiliated with rural preservation organizations in Orange and Sullivan counties. Its portfolio stretches from Newburgh to Tannersville and includes housing for seniors, artists, families, first-time homebuyers, people with disabilities, and those who have experienced homelessness. Despite requests to expand into Westchester, Rockland, and the Capital Region, O’Connor believes the organization has found a sensible footprint.
“There’s an identity to the Mid-Hudson River Valley,” he says. “To do the work we’re doing—helping people buy homes, providing multifamily housing, providing our own property management and facilities—you need geography that makes sense.”
The Project That Changed RUPCO
When asked which development most altered RUPCO’s ambitions, O’Connor names several. The restoration of the Kirkland Hotel in Uptown Kingston was on the organization’s agenda when he arrived. The community had raised about $15,000 toward saving the beloved local landmark; completing the $4.7 million project ultimately required 16 funding sources. The restored Kirkland, which reopened in 2008 with offices and eight apartments, demonstrated RUPCO’s capacity to combine affordable housing, historic preservation, and community memory.
But Woodstock Commons changed the game.
The project began with a request from Woodstock, which had spent decades trying to create affordable housing. RUPCO found a 28-acre site within walking distance of the village, served by municipal water and sewer and zoned for more than 200 units. The town’s comprehensive planning process had identified it as perhaps Woodstock’s last viable opportunity for affordable housing.
The proposal still spent five years before the planning board. A full decade passed between the first phone call and the opening of Woodstock Commons in 2013, with 53 apartments for seniors, families, and artists.
The public opposition was relentless. Critics raised concerns about wetlands, traffic, taxes, property values, and the character of the community. O’Connor had encountered similar reactions earlier in his career, including residents arriving at a meeting about transitional housing at the former Hudson River Psychiatric Center shouting predictions of violence and social collapse.
Woodstock Commons taught him both the value and the cost of persistence. “It was never going to be if,” he says. “It was only a matter of when.” Still, he adds, “I would never bring a project to this organization to be tied up in any town for 10 years again.”
Since the development opened, a number of former opponents—including elected officials—have approached RUPCO to apologize. The same happened after the opening of Landmark Place, the conversion of Kingston’s former city almshouse into supportive senior housing. “No RUPCO” signs had dotted nearby lawns during that project’s approval process.
O’Connor believes opposition to affordable housing has diminished as the housing shortage has spread across income levels and family structures. The need is no longer remote or theoretical. People see their children unable to remain in the communities where they grew up, their parents struggling on fixed incomes, and their coworkers commuting long distances because they cannot afford to live near their jobs.
“They are seeing, feeling, and tasting the lack of affordable housing in very personal ways,” he says. “It’s for my kids. It’s for my parents. My sister needs housing.”
Sixteen Ways to Say Yes
Reduced opposition has not made affordable housing easy to produce. Each development arrives with its own assortment of problems: wetlands, contamination, floodplains, soil conditions, adjacent uses, inadequate infrastructure, restrictive zoning, escalating construction costs, and limited public funding.
Financing often resembles an elaborate stacking exercise. The Kirkland needed 16 sources. The federal Low-Income Housing Tax Credit, created in 1986, has become the country’s primary tool for producing affordable rental housing, but developers cannot use those credits themselves. They sell them to investors, frequently banks seeking to satisfy Community Reinvestment Act requirements. The price investors are willing to pay fluctuates, producing funding gaps that must be filled elsewhere.
The Cold Spring Apartments project currently under construction in Tannersville nearly fell into one of those gaps. RUPCO was invited to the mountaintop community because local restaurants, stores, and Hunter Mountain were struggling to attract workers who could afford to live nearby. The nonprofit acquired the remains of the Cold Spring Hotel, within walking distance of Main Street, and secured competitive tax credits and $2.5 million through Tannersville’s Downtown Revitalization Initiative award.
Then RUPCO struggled to find a tax-credit investor. Tannersville sat outside the preferred Community Reinvestment Act territories of several banks, making an otherwise well-supported project unattractive to them. M&T Bank eventually stepped in, allowing construction to proceed on 56 apartments for seniors and working people. “Absent M&T Bank, that project would not be built,” O’Connor says.
The economics also favor scale. O’Connor once developed an eight-unit tax-credit project in Poughkeepsie; today, he says, such a small development would be nearly impossible. Competitive tax-credit projects generally need around 50 apartments, while other financing structures may favor 100 or even 200. That creates an uneasy equation for rural communities, where large projects may be financially workable but incompatible with the scale of the place.
Water and sewer infrastructure pose another formidable constraint. Much of the Hudson Valley lacks municipal systems in the locations where housing could be built. Existing infrastructure needs billions of dollars in repairs, even before communities contemplate expansion. Zoning often fails to align with the land that does have water, sewer, transportation, jobs, and services.
The shortage has deep roots. Home construction plummeted after the 2008 financial crisis and never fully recovered. Investors purchased foreclosed houses and converted many into rentals, removing them from the homeownership market. Average household size declined, meaning more homes were needed to house the same number of people. Short-term rentals absorbed long-term housing, while remote work made the Hudson Valley accessible to households earning metropolitan-area salaries. Construction, interest, and insurance costs rose sharply after the pandemic.
Yet O’Connor rejects the suggestion that affordable housing is impossible in some communities. “All communities can build it, and it’s needed,” he says. “It’s at a different scale, for sure.”
The design, he argues, should reflect that scale. On a Kingston block dominated by two-story houses with pitched roofs and raised front porches, RUPCO once used four modular sections instead of two, so new homes would match their neighbors. The decision cost more, but avoiding the visual jolt of an incongruous building mattered.
That attention to design also reflects O’Connor’s childhood experience. Willow Landing, RUPCO’s conversion of the former Quality Inn in the Town of Ulster alongside the Thruway, will provide more than 80 supportive apartments for families and individuals who have experienced homelessness. The development employs trauma-informed design and includes a saltwater pool, childcare operated by the YWCA, and a commissary kitchen open to residents and the broader community. “I’m not putting kids in places where they’re going to be embarrassed to live,” O’Connor says. “It’s not going to happen under my watch.”
The Look of Safety
The effect of stable housing can be difficult to express through statistics. O’Connor saw it at Silver Gardens in Highland, RUPCO’s 57-apartment development for seniors, including 29 homes reserved for people who had experienced or were at risk of homelessness.
At an early gathering, residents rushed to thank him. O’Connor redirected them toward the staff members who would be helping them every day, but he could read what the residents had endured on their faces. “There was a mix of trauma from where they had been coming from, tremendous gratitude, and, thirdly, fear that it wasn’t real and they were going to lose it,” he says.
Two women now living in RUPCO developments had each spent three years living in a car. At Landmark Place and Silver Gardens, they have permanent apartments and on-site support. Those outcomes keep O’Connor and his staff engaged through the funding applications, public hearings, environmental reviews, closing delays, and daily work of managing housing.
RUPCO has also attempted to take care of the people doing that work. The organization recently adopted a four-day workweek, moving employees to four eight-and-a-half-hour days without cutting salaries. The change was intended to address burnout in a field that asks staff members to confront homelessness, poverty, housing instability, and bureaucratic obstacles every day. Early employee responses have been strongly positive, and RUPCO is studying whether productivity has changed.
The workload is unlikely to diminish. O’Connor calls for new financing and construction models, expanded job training for the building trades, zoning reform, stronger code enforcement, and enormous investments in water, sewer, and transportation. Government, private business, and nonprofits all have roles to play, he says, because no single sector can resolve a crisis produced over decades.
At 45, RUPCO remains an organization in motion. O’Connor says retirement will come eventually, but he is still drawn to communities that organize around a need and ask RUPCO to help. In Pine Hill, a group of residents raised $500,000 to purchase the deteriorated Wellington Hotel, then approached RUPCO about transforming it into 11 workforce apartments with a cafe and grocery store.
O’Connor went to the meeting prepared to explain that RUPCO was already too busy. He left having agreed to the project. “They had come together with such verve to pull this off,” he says. “It was a perfect example of local energy and an organically articulated need. That’s the kind of thing we can respond to—and should continue to respond to.”
RUPCO marks its 45th anniversary with “Community Lunch: Home Stories Matter,” a celebration centered on residents, families, and community members whose lives have been changed by safe, affordable housing. The event takes place November 19 from 11:30am to 2:30pm at Novellas in New Paltz.
